Unexpected
Copyright© 2026 by Dark Vision
Chapter 1
Romantic Sex Story: Chapter 1 - My life became a series of unexpected events when my grandfather passed away, and I inherited his businesses. I discovered things about life and sex that changed the way I thought. I learned my family engaged in a lifestyle I couldn’t imagine, but quickly embraced. It’s amazing what you can do when you have wealth. While I didn’t earn what I had, I was able to accept and enjoy it with the help of others. My greatest fear was becoming an asshole and treating others poorly.
Caution: This Romantic Sex Story contains strong sexual content, including Ma/Fa Consensual Fiction Cousins Anal Sex Cream Pie Exhibitionism Oral Sex Safe Sex
I was fifteen when my mother and I received the news of my father’s death. The officers who came to the house informed us that my dad was killed while riding his motorcycle.
Although my parents were still married, my father didn’t live with us. He left Mom and me a few years before his death. I never understood why Dad was the way he was. He could have had anything he wanted, but he chose his lifestyle rather than join my grandfather’s businesses. Dad didn’t disappear from our lives when he left. He provided financial support so Mom could stay home when I was young.
I asked him why he left us, and he said he’d explain one day. Unfortunately, he was killed before we had the conversation.
Dad wasn’t unsuccessful. After high school, he went to college and became an attorney. According to my mom, Dad did well in his firm. Mom said my dad was always a bit on the wild side and felt he missed out on things because they got married so young.
After my dad’s untimely death, Mom received a substantial life insurance payment, my father’s savings, and financial assistance from my grandfather. It allowed her to pay off our house and live comfortably. Mom worked in an insurance office, so money wasn’t a problem. We weren’t rich, but we could afford the things we wanted.
When I graduated from high school, I went to work for my grandfather as an intern in the IT department and went to school. I wanted to get my certifications in network design and security.
My grandfather encouraged me, telling me I could do whatever I wanted. He said he was happy I decided to join his company. My grandfather often told me I was his last living relative and would inherit all the businesses one day. I never met my grandmother because she passed away before I was born, and my grandfather never remarried.
I worked for Henderson Enterprises while attending school for the next few years. I earned my networking certification and took a few business classes. Things were going great, and I received a substantial salary. Because I lived at home, I managed to save money and afford nice things.
I was twenty-two when the doctors discovered my grandfather’s cancer. We sat in the doctor’s office as he gave us Grandpa’s grim diagnosis. I felt tears running down my cheeks while the doctor explained my grandfather’s options and life expectancy. Grandpa put his hand on my shoulder, assuring me everything would be okay.
“Grandpa, I’ll move in to help care for you.”
My grandfather was strong-willed, so I assumed he would protest. I was shocked when he said, “I think that’s a good idea, Jeff. I would love to have you with me.”
“How can you be so calm?”
My grandfather shrugged. “What choice do I have? Jeff, we all die. I have lived a full life and enjoyed success. My greatest joy is having you work with me and be part of my life. I wish your father had joined the companies, but Greg always marched to a different drummer.”
I parked in one of the six spaces in the garage. Grandpa and I walked through the mudroom, past the laundry room, and into the kitchen. He pointed at one of the island counter stools and told me to sit. I watched Grandpa take two glasses and a bottle of bourbon whiskey from the cupboard, pour two fingers of the amber liquid into the glasses, and sit beside me.
“Jeff, we have a lot to do, and we don’t know how long we’ll have to do it. I look forward to having you live here with me because it will give us time together. I prefer to keep the news of my cancer between us for now,” Grandpa said.
“When should I move in?” I asked.
“Is tomorrow too soon?”
I shook my head. “What should I tell Mom? She’s going to wonder what’s happening.”
Grandpa took a sip of his drink. “I think we should explain what’s going on. I’ve always been fond of Marge. We should let her know. Why don’t you call your mother and invite her to dinner? We’ll take her out tonight.”
I called my mother to tell her about dinner. She agreed and asked what time she should be ready. Grandpa said seven, and I told her.
We picked my mother up and drove to Louis’s Chop House, my grandfather’s favorite restaurant. Louis Parsons, the owner, greeted him by name as he led us to a table.
“Louis, do you remember my daughter-in-law, Marge, and Jeff, my grandson?”
Louis shook hands with Mom and me. “Of course, I remember them. I hope you enjoy your evening.”
“Thank you. You have a lovely restaurant,” Mom said.
Louis nodded. “We always welcome Larry and his guests. I’ll send your server over.”
Our server came to the table and asked for our drink orders while a busboy filled our water glasses. We ordered cocktails, and the server left.
“Marge, Jeff, and I need to talk to you,” Grandpa said.
“What’s up, Dad?” Mom said.
After the server gave us our drinks, Grandpa asked her to give us a few minutes. The server nodded and left the table.
“Jeff took me to the doctor’s office today. I have been feeling a bit off and decided to get checked out. Marge, I’ve been diagnosed with cancer. The doctor said there wasn’t much they could do. Jeff offered to move into the house and help me, and I’ve agreed,” Grandpa said straightforwardly.
Mom sat and stared into space. Tears ran down her cheeks as she absorbed the shocking news. Grandpa reached over and placed his hand on Mom’s wrist.
“I don’t know what to say, Dad,” Mom said, her voice cracking with emotion.
“I know, Marge, there isn’t anything to say. This is life, and there’s not much we can do to change it.”
“So, what happens now? Did the doctor give you a treatment plan?” Mom said.
Grandpa shook his head. “No, not yet. They have to run a battery of tests to determine the type and stage of the cancer. Once they know, the doctors will inform us about my treatment options.”
Mom dabbed her eyes with her napkin. “As to your question about Jeff moving in with you, by all means, yes. If there is anything I can do, let me know.”
Mom wasn’t his blood relative, but my grandfather always treated her as part of the family. When the accident killed my father, Grandpa made sure Mom was financially stable. We finished our meal without further discussing my grandfather’s prognosis or the future.
The next day, Mom helped me pack my things into boxes. I moved into my grandfather’s house, taking the guest room on the first floor. Mom came with me, helping me unpack and settle in.
Over the next month, Grandpa and I installed an intercom system to monitor his bedroom from the first-floor guest room where I slept and other locations in the house. We developed a routine and got comfortable with each other.
On Wednesdays, maintenance came to the estate to clean the house, cut the grass, do the landscaping, and clean the pool. Grandpa explained he wanted them there the same day to limit the intrusion. The property was over one hundred acres, but only about five acres were lawns with scattered trees and flowerbeds. The rest was wooded with trails for hiking and riding the Gator UTV.
Grandpa and I would take his thirty-two-foot center console boat out and fish on the lake when the weather permitted. There were other homes, but none near the peninsula the house sat on. Grandpa told me his father purchased the lakefront property outside a small Georgia town. My great-grandfather built the eight-thousand-square-foot house in the nineteen fifties.
There was a boathouse with a rooftop deck above the slips where he kept the boat. The structure was large enough to moor two forty-foot boats side by side, but he only had one.
Grandpa added a seventy-five-by-twenty-five-foot lap pool and a cabana with an apartment on the second floor. He told me he planned to use the two-bedroom apartment for live-in help if he decided to have them. The cabana’s first floor contained two changing rooms with showers, two bathrooms, a sitting area, and an unused space. He also replaced a detached garage with a new sixty-by-thirty-foot pole barn.
The doctors offered different options for treatment. My grandfather told them he would consider his choices and let them know. He said he wasn’t sure he wanted to endure radiation and chemo.
Reality set in when my grandfather’s attorneys and financial advisor came to the house. Grandpa invited them in, and we went to the spacious office. My grandfather’s desk sat near a window with a view of the front yard. There was a conference table with twelve chairs, and two walls covered with bookshelves.
“Jeff, I’d like you to meet Steven Gold and Barbara Quinn. Their firm has been handling my legal affairs for many years. Steven’s father was my father’s attorney. Art Levinson is my financial advisor and takes care of the money.
“I’d also like you to meet Ellen Baxter. Ellen is my personal assistant and handles almost everything for me. She’s worked for me for the past twenty years. If you need to know anything about Henderson Enterprises, she can help you,” Grandpa said.
I shook hands with everyone and sat at the conference table in the office. Steven, Barbara, and Art sat across the table from Grandpa, Ellen, and me. They opened their briefcases and removed several thick folders.
“Larry, I speak for all of us when I say we’re shocked and heartbroken about your news. Please be assured we will do everything possible to help you,” Steven said.
I looked at Ellen, noticing tears in her eyes. Grandpa patted her hand and smiled. She nodded as tears rolled down her cheeks.
“Thank you, Steve. I know you and your firm will help Jeff with the transition. There are no secrets regarding my personal or business dealings. He needs to know as much as possible about everything.” Grandpa smiled. “Does anyone want something to drink before we get started?”
We all agreed on coffee, so I left the office, went to the kitchen, and prepared a tray with mugs, creamer, sweetener, and a carafe of fresh coffee. When I returned, Ellen helped me serve our guests.
“Where would you like to start, Larry?” Barbara said.
“I think I should give Jeff a little history of the companies. Your great-grandfather started Henderson Enterprises in the nineteen twenties. He hand-made special items for the medical industry...” Grandpa began.
Over the next few hours, I learned how my great-grandfather and grandfather built and grew the companies from a tiny shop to over ten plants, five distribution centers, and offices around the country and in Europe. Additionally, there was Henderson DME. The division had retail outlets providing durable medical equipment in most major cities. Henderson Enterprises’ sales were over twenty billion dollars a year.
“I knew the company was huge, but I had no idea how big it was,” I said when my grandfather finished.
“Henderson Enterprises is a privately held company, and Larry’s holding company, Henderson Investments, owns one hundred percent of the stock. Henderson Investments has real estate properties and owns several other businesses. We have created a living trust and transferred all his stock into it. We are placing all of his assets, other than his vehicles, in the trust,” Steve said.
“Larry also has a substantial personal investment portfolio. We are in the process of moving everything into the new trust. The living trust provides certain tax advantages and makes transferring ownership easy. Larry is the trustee and controls the trust,” Art said.
I guess my grandfather could see my confusion. He smiled and said, “You will become the trustee when I die. When the day comes, you can do whatever you want with the companies and other assets.”
Taking a deep breath, I felt tears forming. Grandpa put his hand on my shoulder, squeezed me, and smiled.
“What do you want me to do with the companies?” I asked.
“Jeff, I want you to do whatever you feel best. The businesses have provided for my employees and me for many years. The C-level management team runs the companies, so I don’t have much involvement in the day-to-day operations any longer.”
“Why haven’t you sold the companies?”
“Your grandfather has received offers for Henderson Enterprises. We reviewed them, but felt they didn’t fit Larry’s philosophies. They didn’t guarantee the employees would be retained or treated as Larry felt necessary,” Stephen said.
“The best fit would be to find a private equity firm to purchase Henderson Enterprises and retain the management and employees,” Barbara said.
“I don’t understand any of this,” I said.
Grandpa chuckled. “Jeff, you’ll find a wise man knows what he doesn’t know or understand. That’s why we hire people who do. I trust my legal team and Art’s firm to handle these things.”
We spent a few hours discussing the company structure and Grandpa’s management teams. I learned that while my grandfather didn’t involve himself in most day-to-day operations, he still stayed close to what happened with the companies. The attorneys and Art assured me they would help me with anything I needed. As we talked, I realized how little I knew about the companies, even though I worked there.
Grandpa asked Ellen, Stephen, Barbara, and Art to meet every Wednesday. During our weekly meetings, I learned more about the companies. I discovered that Henderson Enterprises owned two planes, including a Gulfstream G550, like the one on the television show Criminal Minds. Grandpa told me he didn’t like using commercial airlines when traveling to their facilities.
A few months later, Grandpa asked Ellen to arrange a meeting with all C-level officers. He wanted to inform them of his condition and discuss the future of Henderson Enterprises. At the meeting, Grandpa told the group that he had been diagnosed with terminal cancer. After the murmurs died down, he explained his plans for his companies. Grandpa introduced Stephen, Barbara, Art, and me. Many of the managers knew me. The ones who didn’t were surprised my grandfather would pass the companies to me.
Stephen took over, telling the group there were no changes planned and that the C-Level personnel would maintain their titles, positions, and responsibilities. After dismissing everyone except the division vice presidents, Grandpa told his senior managers they would join the company’s board of directors, and Stephen, Barbara, Art, and I would also be board members.
As everyone left, Grandpa asked the company president, Peter Jackson, to remain. We sat at the table while the other C-level personnel left the room, leaving Ellen, the legal team, and me.
“Peter, when it’s time, you’ll become the CEO and run the company. I want you to do whatever you can to aid Jeff in his decisions regarding the companies,” Grandpa said.
“You know you can count on me, Larry,” Peter said.
Grandpa lost his battle with cancer a year and a half after the doctors diagnosed him. I spent as much time as possible with him during the last months of his life. Mom would come over after work to help me make our meals while teaching me how to cook. We hired a home-care service for the last four months.
Over two hundred people attended the memorial service. The chapel was filled to capacity as Grandpa’s friends eulogized his life. After the service, everyone was invited to a luncheon. Most of the people attended the luncheon at Louis’s Chop House. The owner closed the restaurant in honor of Grandpa. While we ate, Mom stayed by my side, offering comfort.
As the luncheon ended and the guests began leaving, Ellen approached me. She hugged me and expressed her sympathy.
“Jeff, if you need anything, please let me know. Larry was an extraordinary man, and I will miss him. It’s been an honor working with him,” Ellen said.
“Thank you, Ellen. Grandpa spoke highly of you.”
Ellen nodded, hugged me again, and left. Mom and I remained until the last guest departed, then went home. She invited me to her home, but I told Mom I wanted to go to Grandpa’s, now my house.
Even though I knew my grandfather would die, nothing could have prepared me. My sorrow consumed me for several days after the service. It took a couple of weeks to recover enough to begin taking care of things for the businesses.
I called for a meeting with Stephen, Barbara, and Art. We sat in the office at the house, making plans for the future. When Art explained the trust’s holdings, I realized I was a billionaire. We would let the board of directors run Henderson Enterprises. With the help of the team, I would learn and run Henderson Investments.
After my grandfather’s passing, I walked into his bedroom, shook my head, and decided to make a few changes. After consulting with Art, I hired an architect to remodel my house. I donated most of the furniture and the hospital bed.
When Hugh Davis, the architect, asked what I had in mind, I told him the entire house needed updating except for the billiard room and Grandpa’s office. Those two rooms would remain the same. I wanted something more modern and the latest technology for the rest of the house. Hugh spent two weeks coming up with a design I liked. Once I agreed to the plan, Hugh hired a general contractor.
During the renovations, I decided to stay with my mom. One evening in early May, I ran into my high school girlfriend, Anne Marston, while Mom and I were at a restaurant for dinner. Anne and I dated during our senior year, went to prom together, and became lovers. I smiled when she said hello, remembering the night we shared our virginity.
Anne and I dated during the summer after graduation. We drifted apart when she went to college in a different state. She was my only girlfriend.
Mom said hi, telling Anne she remembered her from when we dated.
“Hi, Anne. How have you been?” I said.
“I’m doing well, Jeff. I’m working here while I’m home for the summer. I’ll begin my master’s degree in the fall. How are you doing?”
“Things are great. I work for Henderson Enterprises in the IT department.” I didn’t feel that telling Anne I owned the company was necessary.
During dinner, we chatted when we could. When Anne brought the check, she gave me a note with her phone number. “Call me if you’d like to get together and catch up.”
I paid the bill, told Anne I’d talk to her later, and left the restaurant. When I got into the car, I noticed the grin on Mom’s face.
“What?” I said.
“You should ask Anne out, Jeff,” Mom said.
“I don’t know. It’s been a long time, Mom.”
“It’s been too long, Jeffery. You haven’t done anything besides work, school, and care for your grandfather for a long time. It’s time to get out and socialize with people your age.”
“I’ll think about it, Mom.” I wondered if Anne and I could pick up where we left off.
I was on my way to Mom’s house from my home. As I did most days, I stopped to check the progress and talk with the general contractor. The project was coming along well and was on schedule. I used my cell phone to call Anne.
“Hi, Jeff. I wondered if you’d call me,” Anne said when I said hello.
“I was thinking about what you said about getting together. Would you like to go out one of these evenings?”
“Yes, I’d enjoy seeing you again. If you’re free this Friday, I have it off.”
“Friday sounds good to me. I’ll pick you up at seven. We’ll go to a nice restaurant for dinner.”
“Perfect. See you then.”
On Friday evening, I got into my Lincoln and headed for Anne’s house. When I knocked on the door, Mr. Marston opened it and invited me in. We chatted for a moment while I waited for Anne.
Anne came into the living room and said, “Hi, Jeff. Are you ready to go?”
“Yes, I’m ready. You look great.”
Anne wore a knee-length skirt and a blouse. “Thanks, you look good, too.”
I wore dress slacks, a white shirt, and a sports jacket.
After saying goodbye, we left the house. I closed the door for Anne when she got into the car.
During our ride to the restaurant, we chatted. Anne told me she was doing well in college and would receive her master’s degree in finance when she graduated. I told her about working in the IT department at Henderson Enterprises. I didn’t work at the company, but I didn’t want to tell Anne any details of my life for the past few years.
At the restaurant, the host greeted me by name. I’d been there many times with my grandfather, and most of the employees knew me. The host showed us to the reserved table, pulling out Anne’s chair when he seated us.
Anne smiled. “I take it you’ve been here before.”
“I have. I used to come here with my grandpa.”
During dinner, we caught up on our lives. Anne told me about school and her classes. When I told her my grandfather had passed away, she said she was sorry.
“So, are you dating?” Anne said.
“No, I haven’t been seeing anyone. How about you?”
“I’ve dated at school, but don’t have time for a full-time relationship with a man. My classes are hard, so I spend a lot of time studying. I also have a part-time job. School and living in California are expensive. Because I have to work, it’s taking longer than normal to get my degree.”
We had wine with our dinner. Anne mentioned how good the chicken dish she ordered tasted. While we ate, sipped our wine, and talked, I couldn’t help remembering when we had sex. Both of us were virgins and lacked experience. Our couplings were usually in the car, but we used a bed several times.
“Dinner was great,” Anne said as I held the car door for her.
“I’m glad you enjoyed it. What would you like to do now?”
“Do you know anywhere we can go dancing?”
“Not really. The last time I danced was at our prom.”
Anne took out her phone and started looking for a place to dance. She told me there was a club near her house where we could go. I followed her directions as I drove.
Anne slipped her arm through mine, found a table, and sat down when we entered the club. A server came over and took our drink orders.
“Come dance with me,” Anne said after sipping her wine.
We went to the dance floor and began moving to the fast music. After a few songs, a slow number came on, and we danced with our bodies pressed together.
“I remember how well you danced at our prom. I guess you haven’t lost it,” Anne said.
“As I said, it was the last time I danced. I guess the lessons I had paid off.”
Pulling her head back, Anne looked into my eyes. “You took dancing lessons?”
“Yeah, I didn’t want to embarrass myself at the prom, and I wanted you to have a good time.”
“I had a great time at the prom. It was even better after the dance.”
I couldn’t help chuckling as I remembered our night in a motel room. It was only the third time we had had sex, and the first time in bed. It was much better than in the car.
“It was fun, wasn’t it?” I replied.
Anne put both hands on my head, pulled my mouth to hers, and kissed me. When I felt her tongue, I parted my lips to accept it. We held the kiss for several moments before she pulled back and gazed into my eyes.
“You’re still a good kisser, Jeff.”
“Thanks, so are you.”
We finished our dance and went back to the table. While sipping our drinks, we shared smiles as I wondered if Anne was interested in picking up where we left off seven years ago.
Anne and I decided to dance and returned to the dance floor. As soon as a slow song started, she pressed her body against mine, and we kissed. I bent down because I was five inches taller than her five-foot-six frame. Anne shifted, moving her hip against my crotch.
“Let’s get out of here.” Anne nuzzled my neck.
We finished our drinks and left the club. As soon as we were in my car, Anne lifted the armrests, slid next to me, grabbed my head, pressed her mouth to mine, and stuck her tongue into my mouth.
As I returned Anne’s aggressive kiss, I put one of my hands on her breast and massaged her small, firm mound, causing her to moan.
“We need to find someplace private. Do you think kids still park at the old gravel pit?” Anne said.
“Probably, but I have a better idea. Let’s go to my house.”
“What about your mom?”
“Anne, we’re twenty-five, not eighteen. Mom won’t mind us watching television in the basement.”
“I don’t care if you don’t.”
I pulled into the pharmacy parking lot on the way to my mom’s house. “I’ll be right back,” I said.
I grabbed a box of condoms in the store, paid for them, and returned to the car. Anne snuggled against my side as I headed for the house and rested her hand on my leg, moving it just above my knee.
Mom was sitting in the living room when we came in. “Hi, Mom. Anne and I are going to watch television in the rec room.”
“Okay, I’m going to bed shortly. See you in the morning. It’s nice to see you again, Anne. How have things been?”
“Everything is great, Mrs. Henderson,” Anne said.
“You two have fun. I’ll talk to you later.”
Anne and I went downstairs, turned on the television, found a movie, and adjusted the volume.
Anne sat on the couch, curling her legs under her. After I removed my sports coat, I sat next to her. We came together and began kissing while we ran our hands over one another. I rubbed her breasts for a moment, then started unbuttoning her blouse.
Anne’s blouse was off a few moments later, as was her bra. When we dated, she would complain about the size of her small breasts, but didn’t say a word about them as I ran my thumb over the nipple of her apple-sized mound.
“I always loved how you played with my boobs. You never squeezed them too hard or hurt me.”
Anne moved her hands to my waist, undid my belt, unbuttoned my slacks, and lowered my zipper as she talked. Reaching into my pants, Anne rubbed my cock through my boxer briefs for a moment, then, using her other hand, she pulled the waistband away and slipped her hand into my underwear.
I lifted my butt off the couch and lowered my slacks and underwear. Anne wrapped her hand around my shaft, stroking me as I tangled my fingers in her dark, shoulder-length hair, pulled her mouth to mine, and resumed kissing.
Moving, Anne knelt on the couch, leaned over, and took my cock into her mouth. I let out a muffled groan as I experienced my first blowjob. When we dated, Anne and I didn’t engage in oral sex. I wanted to, but she said she wouldn’t do it. It appeared Anne had overcome her reluctance.
Anne bobbed her head on my cock while I rubbed her back, moving my hand to her ass. She wiggled as I pulled her skirt up to her waist. When I ran my hand over her bottom, she moaned around my dick.
Lifting her head from my lap, Anne kissed me. I continued stroking her ass while we flicked our tongues together. After a few minutes, we separated, and Anne removed her skirt. We finished undressing and hugged each other.
I kissed my way to Anne’s breasts, taking time to suck each of her nipples. She ran her fingers through my hair, then pushed down on my head.
“Will you lick my pussy?”
“Sure. I guess you’ve overcome your aversion to oral sex.”
“Yeah. I didn’t want to do it when we dated because I felt you’d think I was nasty.”
Anne stretched out on her back, opened her legs, and guided my head to her crotch. I looked at her, noticing she was shaved. Unsure of how to proceed, I licked her crotch while she ran her fingers through my hair, moaning as I explored.
I looked up at Anne. “I’ve never done this before.”
Anne told me what she liked, and I fulfilled her wishes. Anne moaned, telling me to finger her pussy. I complied, sliding two of my digits into her wet vagina. After about fifteen minutes of my oral attention, Anne grabbed the back of my head, pressing it into her crotch as she came.
When Anne’s arms flopped next to her body, I moved up. She smiled, pulled my mouth to hers, and we kissed. I reached for my slacks, removed the package of condoms from my pocket, and took one out of the box. Anne peppered my face with kisses as I encased my rigid cock in latex.
I gripped my shaft and rubbed my cock up and down through her slit. She reached between us, took my cock, and placed it at her entrance. Anne exhaled as my cock slid into her pussy, and I started moving, thrusting my dick in and out of her.
Anne hooked her legs over my thighs, humping against me as I fucked her. Unlike when we dated, Anne was active, participating in our coupling. Internet research and hours of practice while masturbating gave me the staying power I didn’t possess in the past. I was lucky to last more than ten minutes during our previous times, even the second time we fucked the same night.
After about twenty minutes of steady fucking, Anne told me to get up, got on her hands and knees, then wiggled her ass at me. I moved closer, put my cock back into her pussy, and experienced my first doggy-style fuck. As I slid into Anne, she pushed back.
“Damn, you feel good. Fuck me harder, Jeff,” Anne said, breaking her silence.
Anne swayed her back, reached under her body, and rubbed her clit while I gripped her narrow hips. I ran one hand up her side, clutching her breast while fucking her.